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    220497-79-0

    Catalog No. EBD43305

    CAS 220497-79-0

    Name Fmoc-2-bromo-D-phenylalanine

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    Basic Information

    Synonyms: (R)-N-FMOC-2-Bromophenylalanine Fmoc-D-2-Bromophenylalanine Fmoc-2-Bromo-D-phenylalanine N-(9-Fluorenylmethoxycarbonyl)-2-bromophenyl-D-alanine

    Molecular Formula: C24H20BrNO4

    Molecular Weight: 466.32

    MDL Number: MFCD01311770

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

    Product Description:
    Fmoc-D-2-Bromophenylalanine is a non-natural, side-chain modified amino acid derivative. It features a 2-bromophenyl group on the beta-carbon of the phenylalanine side chain and is protected at the N-terminus with a 9-fluorenylmethoxycarbonyl (Fmoc) group. The presence of the D-configuration at the alpha-carbon makes it a chiral building block. This compound is primarily used as a specialized amino acid building block in solid-phase peptide synthesis (SPPS) employing the Fmoc strategy. The bromine atom on the aromatic ring serves as a versatile chemical handle for further functionalization via cross-coupling reactions (e.g., Suzuki, Sonogashira) after peptide assembly, enabling the introduction of diverse biophysical probes, labels, or to modulate peptide properties. It is crucial in medicinal chemistry and chemical biology for the synthesis of peptide-based drug candidates, peptidomimetics, and research tools where site-specific modification is required. The bromophenylalanine moiety can be incorporated to study protein-protein interactions, develop constrained peptides, or create novel materials. Its use allows for the precise engineering of peptide structure and function, making it a valuable reagent in the development of targeted therapeutics and diagnostic agents.
    Physical Properties

    Melting Point: 140 °C

    Boiling Point: 657.1 °C at 760 mmHg

    Flash Point: 351.2 °C

    Density: 1.459 g/cm3

    Storage: Store at 0°C

    Analytical Data

    Appearance: white powder

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